Lifelong entrepreneur: There's one way to ensure you never fail at starting a business


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Ivan Gushchin/Strelka Institute/Flickr

Keep the cost of failure low.

At 39, Chris Guillebeau says he's never held down a "real" job.


That's because the New York Times bestselling author has worked for himself in various capacities for the last 20 years, most recently as an international speaker, blogger, podcast host, and workshop instructor.

Autonomy is important to Guillebeau, and he believes it's something everyone can achieve during their career, whether you quit the 9-to-5 grind to launch a startup or dedicate some free time to build a side hustle.

No matter the venture, he told Business Insider, "people always have fear about risk," mainly if they're sinking money into it. Ultimately, he says, there's one way to ensure you won't waste time or money: Keep the cost of failure low.

In other words, you can achieve success without high stakes.


"If the cost of failure is low and you try something that doesn't work out, is it really a failure? Or is it more like, 'Oh I just did that and now I'll try something else and learn from that process and I'll go onto something different,'" he said.

"I wrote a book called 'The $100 Startup,' and the whole thesis of that book is that entrepreneurship doesn't need to be risky and you shouldn't actually beg for money or put everything on your credit card or go for investors," he explained. "You should figure out how you can start something without spending a lot of money."

In researching the 2012 bestseller, Guillebeau sourced 1,500 business owners earning a baseline profit of $50,000 a year, where the initial investment was $1,000 or less. In many cases, it was less than $100. From there, he chose 50 of the most compelling stories to analyze and he crafted a guide to starting a lucrative business on the cheap. The book reveals that it's as simple as using your expertise or passion to create a product or service that people are willing to pay for - and the profits will follow.

Guillebeau now focuses on side hustles and coaching others on how to generate extra income without quitting their day job. He says there's even more opportunity under these circumstances to embrace risk and be willing to experiment.

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